Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole

A palladium-catalyzed three-component reaction between 5-(2-chloroquinolin-3-yl) oxazoles, isocyanides, and water to yield 3-(oxazol-5-yl)quinoline-2-carboxamides is described. Interestingly, sulfonylation occurred when the same reaction was performed with toluenesulfonylmethyl isocyanide (TosMIC) a...

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Autores principales: Yasaei, Zahra, Mohammadpour, Zeinab, Shiri, Morteza, Tanbakouchian, Zahra, Fazelzadeh, Shima
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6587330/
https://www.ncbi.nlm.nih.gov/pubmed/31259168
http://dx.doi.org/10.3389/fchem.2019.00433
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author Yasaei, Zahra
Mohammadpour, Zeinab
Shiri, Morteza
Tanbakouchian, Zahra
Fazelzadeh, Shima
author_facet Yasaei, Zahra
Mohammadpour, Zeinab
Shiri, Morteza
Tanbakouchian, Zahra
Fazelzadeh, Shima
author_sort Yasaei, Zahra
collection PubMed
description A palladium-catalyzed three-component reaction between 5-(2-chloroquinolin-3-yl) oxazoles, isocyanides, and water to yield 3-(oxazol-5-yl)quinoline-2-carboxamides is described. Interestingly, sulfonylation occurred when the same reaction was performed with toluenesulfonylmethyl isocyanide (TosMIC) as an isocyanide source. The reaction with 5-(2-chloroquinolin-3-yl)oxazoles and TosMIC in the presence of Cs(2)CO(3) in DMSO afforded 5-(2-Tosylquinolin-3-yl)oxazoles. In basic media, TosMIC probably decomposed to generate Ts(−) species, which were replaced with Cl(−). Tandem oxazole formation with subsequent sulfonylation of 2-chloroquinoline-3-carbaldehydes to form directly 5-(2-tosylquinolin-3-yl)oxazoles was also investigated.
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spelling pubmed-65873302019-06-28 Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole Yasaei, Zahra Mohammadpour, Zeinab Shiri, Morteza Tanbakouchian, Zahra Fazelzadeh, Shima Front Chem Chemistry A palladium-catalyzed three-component reaction between 5-(2-chloroquinolin-3-yl) oxazoles, isocyanides, and water to yield 3-(oxazol-5-yl)quinoline-2-carboxamides is described. Interestingly, sulfonylation occurred when the same reaction was performed with toluenesulfonylmethyl isocyanide (TosMIC) as an isocyanide source. The reaction with 5-(2-chloroquinolin-3-yl)oxazoles and TosMIC in the presence of Cs(2)CO(3) in DMSO afforded 5-(2-Tosylquinolin-3-yl)oxazoles. In basic media, TosMIC probably decomposed to generate Ts(−) species, which were replaced with Cl(−). Tandem oxazole formation with subsequent sulfonylation of 2-chloroquinoline-3-carbaldehydes to form directly 5-(2-tosylquinolin-3-yl)oxazoles was also investigated. Frontiers Media S.A. 2019-06-14 /pmc/articles/PMC6587330/ /pubmed/31259168 http://dx.doi.org/10.3389/fchem.2019.00433 Text en Copyright © 2019 Yasaei, Mohammadpour, Shiri, Tanbakouchian and Fazelzadeh. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Yasaei, Zahra
Mohammadpour, Zeinab
Shiri, Morteza
Tanbakouchian, Zahra
Fazelzadeh, Shima
Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole
title Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole
title_full Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole
title_fullStr Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole
title_full_unstemmed Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole
title_short Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole
title_sort isocyanide reactions toward the synthesis of 3-(oxazol-5-yl)quinoline-2-carboxamides and 5-(2-tosylquinolin-3-yl)oxazole
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6587330/
https://www.ncbi.nlm.nih.gov/pubmed/31259168
http://dx.doi.org/10.3389/fchem.2019.00433
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